The home is about 8 years old, so the up keep is low and a hail storm just allowed me to put a brand new roof on it at no cost.  

For starts, I will run the financials for any property to ensure that it can carry its own weight, i.e. pay for itself.  

$20k in the whole probably feels like a huge weight, but honestly its not that bad.  

An investor savvy real estate agent is worth their weight (and commission) in gold.

Finally, they do a reconciliation where they compare these values and give weight to the one that is most significant. 

I bought the property with a new roof, new flooring, and new appliances, vastly reducing my upkeep. 

This is shifting the burden of up keeping the infrastructure from the town to the investor which is probably good in the eyes of the town. 

He is a cop, most have superiority complexes and like to push their weight around.

I didn't put high end finishes on it, but we did put some decent upgrades in it (with the mindset of resell value, etc.)The home requires very minimal landscaping/outdoor upkeep, while still being a SFH, which is one thing we really liked.

Seems like unecessary extra weight.